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Arie Crown Theater
Located in the McCormick Place Convention Center, the recently refurbished Arie Crown Theater features a variety of performances, from pop concerts to lectures to touring Broadway production shows.
2301 S Lake Shore Dr Tel 312.791.6516

Bailiwick Arts Center
Consisting of three separate theaters, the Bailiwick hosts more productions than any other theater in Chicago. Works range from contemporary to adapted classics to experimental, and the annual gay-themed Pride Series is always popular.
1229 W Belmont Ave Tel 773.883.1090

Chicago Shakespeare Theater
Located in the middle of Navy Pier just off of Lake Shore Drive, the Chicago Shakespeare Theater performs from October through June.
Navy Pier Tel 312.595.5600

Civic Opera House
Located on the west side of the Loop, the Civic Opera House if the home of the Chicago Lyric Opera. The performances are held in the base of the 45 story combined use skyscraper. The season of the Chicago Lyric Opera generally lasts from September through February.
20 N Wacker Dr Tel 312.409.3032

Second City
A Chicago institution for more than 40 years, Second City has launched the careers of many famous comedians, including John Belushi, Bill Murray, and Chris Farley.  The sketch and improv comedy shows are consistently topnotch, and audience participation is encouraged.  Second City also features a smaller theater, called e.t.c., that tends to offer edgier material.
1616 N Wells St Tel 312.337.3992

Steppenwolf Theatre Company
Well-known for the quality of its acting ensemble (including such actors as co-founder Gary Sinise and John Malkovich), the Steppenwolf Theatre Company has featured cutting-edge contemporary American theater for more than 25 years. The current state-of-the-art location includes a 500-person mainstage and a smaller studio theater, which offers more experimental works and productions from other theater companies.
1650 N Halsted Tel 312.335.1650

Symphony Center
Home of the Chicago Symphony Orchestra, the Symphony Center also plays host to touring orchestras, jazz combos, and world music events. In addition, the center contains Echo, an interactive learning center about music geared towards children, and Rhapsody, a high-end modern American restaurant.
220 S Michigan Ave Tel 312.294.3000